Efficient synthesis of 2-amino-4-aryl-8-[(E)-arylmethylidene]-5, 6, 7, 8-4H pyrano [3, 2-c]pyridine in green media

被引:4
作者
Balalaie, Saeed [1 ]
Mehrazar, Mehrdad [1 ]
Haghighatnia, Yaghoub [1 ]
机构
[1] KN Toosi Univ Technol, Peptide Chem Res Ctr, Tehran, Iran
关键词
tetrahydro-4H-pyrano [3; 2-c]pyridine-3-carbonitriles; green media; diammonium hydrogen phosphate; piperidine; ring closure; atom-economy; condensation reaction; DIAMMONIUM HYDROGEN PHOSPHATE; ONE-POT SYNTHESIS; DIELS-ALDER REACTION; ORGANIC-REACTIONS; AQUEOUS-MEDIA; SOLVENT-FREE; WATER; DERIVATIVES; CYCLOADDITION; VERSATILE;
D O I
10.1080/17518253.2012.709280
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
An efficient, general, and atom-economic procedure for the synthesis of 2-amino-6 methyl-4-aryl-8-[(E)-arylmethylidene]-5, 6, 7, 8-4H-pyrano [3, 2-c]pyridine-3-carbonitriles has been developed by reaction of 3,5-bis[(E)-arylmethylidene]-tetrahydro-4(1H)-pyridinones with malononitrile. The reaction proceeds under green media (EtOH/H2O, 1:1) and in the presence of diammonium hydrogen phosphate (10%) or piperidine (10%) to afford pyranopyridines at room temperature with good high yields. [GRAPHICS] .
引用
收藏
页码:101 / 105
页数:5
相关论文
共 44 条
[1]   Novel and efficient catalysts for the one-pot synthesis of 3,4-dihydropyrano[c]chromene derivatives in aqueous media [J].
Abdolmohammadi, Shahrzad ;
Balalaie, Saeed .
TETRAHEDRON LETTERS, 2007, 48 (18) :3299-3303
[2]   An efficient green chemical approach for the synthesis of structurally diverse spiroheterocycles with fused heterosystems [J].
Arya, Anand Kumar ;
Kumar, Mahendra .
GREEN CHEMISTRY, 2011, 13 (05) :1332-1338
[3]   Diammonium hydrogen phosphate as a versatile and efficient catalyst for the one-pot synthesis of pyrano[2,3-d]pyrimidinone derivatives in aqueous media [J].
Balalaie, Saeed ;
Abdolmohammadi, Shahrzad ;
Bijanzadeh, Hamid Reza ;
Amani, Ali Mohammad .
MOLECULAR DIVERSITY, 2008, 12 (02) :85-91
[4]   Diammonium hydrogen phosphate:: An efficient and versatile catalyst for the one-pot synthesis of tetrahydrobenzo[b]pyran derivatives in aqueous media [J].
Balalaie, Saeed ;
Bararjanian, Morteza ;
Sheikh-Ahmadi, Masoumeh ;
Hekmat, Shohreh ;
Salehi, Peyman .
SYNTHETIC COMMUNICATIONS, 2007, 37 (7-9) :1097-1108
[5]   Novel, efficient, and green procedure for the Knoevenagel condensation catalyzed by diammonium hydrogen phosphate in water [J].
Balalaie, Saeed ;
Bararjanian, Morteza ;
Hekmat, Shohreh ;
Salehi, Peyman .
SYNTHETIC COMMUNICATIONS, 2006, 36 (17) :2549-2557
[6]   Efficient synthesis of 1,4-disubstituted polyfunctional piperazines via a sequential one-pot Ugi/nucleophilic addition five-component reaction [J].
Bararjanian, Morteza ;
Balalaie, Saeed ;
Movassagh, Barahman ;
Bijanzadeh, Hamid Reza .
TETRAHEDRON LETTERS, 2010, 51 (25) :3277-3279
[7]   Six-Component Reactions for the Stereoselective Synthesis of 3-Arylidene-2-oxindoles via Sequential One-Pot Ugi/Heck Carbocyclization/Sonogashira/Nucleophilic Addition [J].
Bararjanian, Morteza ;
Balalaie, Saeed ;
Rominger, Frank ;
Movassagh, Barahman ;
Bijanzadeh, Hamid Reza .
JOURNAL OF ORGANIC CHEMISTRY, 2010, 75 (09) :2806-2812
[8]   Enamine-based aldol organocatalysis in water: Are they really "all wet"? [J].
Brogan, Andrew P. ;
Dickerson, Tobin J. ;
Janda, Kim D. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (48) :8100-8102
[9]   Water: Nature's Reaction Enforcer-Comparative Effects for Organic Synthesis "In-Water" and "On-Water" [J].
Butler, Richard N. ;
Coyne, Anthony G. .
CHEMICAL REVIEWS, 2010, 110 (10) :6302-6337
[10]  
Chakraborti AK, 2007, GREEN CHEM, V9, P1335, DOI 10.1039/b710414f